


The Winchesters in Stars Hallow

by MariLovesFantasy24601



Category: Gilmore Girls, Supernatural
Genre: Alternate Universe - Supernatural (TV) Fusion, Crossover, Dean Winchester Angst, Drama, F/M, Funny, Love, Protective John Winchester, Silly, Supernatural - Freeform, Teen love, Young Sam Winchester, gilmore girls - Freeform, rory gilmore - Freeform
Language: English
Status: In-Progress
Published: 2019-11-06
Updated: 2019-11-05
Packaged: 2021-01-23 21:58:52
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,134
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21327328
Author URL: https://archiveofourown.org/users/MariLovesFantasy24601/pseuds/MariLovesFantasy24601
Summary: The Winchester boys arrive in Stars Hallow for a case, but things take some unexpected twists. One of which is Sam falling in love with a shy girl named Rory.
Relationships: Dean Forester/Rory Gilmore
Comments: 1
Kudos: 5





	The Winchesters in Stars Hallow

**Winchesters in Stars Hallow**

Chapter 1: welcome to stars hallow

Sam and Dean were teens when they first ventured into the unique town, yet simple town of Stars Hallow. It was a small town in Connecticut, just outside of Hartford. The town had a vintage, almost cute look to it. Every inch of the town was clean and surrounded with people who all seemed to know one another. The houses were big and the flowers were in bloom. Each citizen seemed overly content with where they lived.

“Who the hell would want to live here? This place looks like it never came out of the 40s.” Dean commented, as he looked out the window. Dean Winchester was 19, at the time, dressed in Metallica shirt and a leather jacket. He wore dark blue jeans and worn out work boots.

“This place makes me want to puke,” Dean continued. “We need to get in and out of here as soon as possible!”

Sam was 16 at the time, his eyes had been focused on the latest book he was reading. He was dressed in a flannel shirt and light blue jeans. On his feet he wore converse that had more dirt on them then plastic. As he looked out the window, he sighed and slumped in his chair.

_Great another case._ He thought. _More mindless killing, more monsters and another chance for dad to critique everything I do._

“I don’t want to be here anymore then you guys do.” John spoke. “But Annie said there was a case here. 13 people were murdered within 3 weeks. From what she said, its clearly a vampire case. The blood was drain from the victims’ bodies and all of them had weird markings on their necks. Annie and her daughter are scared they might be next.”

“Since when do you care about Aunt Annie?” Dean questioned. “The two of you haven’t spoken to each other in about 15 years and now were racing off to go save her and her kid.”

“They are still family, Dean.” John reminded his son. “I may not get along with her, like I used to, but I’m not going to let them die if I can stop it.”

Sam looked at his brother and father with confusion.

“Who’s aunt Annie?” Sam asked. “Why have I never heard about her before?”

“She is my younger sister.” John revealed. “After your mother died, Annie moved in with us for a few months and helped me to take care of the two of you. She was living in jersey at the time and she dropped everything to help me. I started to research about demons and hunting them, I got the idea to try to kill the creature that took your mother from us. I told Annie what I wanted to do and I asked her if she could take care of you guys on her own while I went hunting….it didn’t go over well with her. We got into a huge fight. She was convinced that I was crazy, she said it wouldn’t work, and if it did go hunting I would get myself killed. She told me I was acting recklessly and selfishly. She claimed I was so focused on revenge that I was putting what I wanted before what the two of you need. When I refused to see things her way, she left town and never spoke to me again. Well that was, until last night when she called my cell phone.“

“Well she wasn’t wrong.” Sam mumbled.

“I did what I had to in order to protect you boys!” john shouted. “There are monsters in this world and they are merciless! They would kill you without even thinking about it! What kind of father would I be if I didn’t teach you how to defend yourself against them!?”

“That’s not the point!” Sam argued. “You put us in danger every day! You make us travel across the country risk our lives to save people we don’t know! What kind of father forces his sons to hunt down monsters!? We never had a choice, it was this or nothing! We’re not even searching for the demon that killed mom anymore! We haven’t had a lead on that in years! So, what’s the point of all this? To kill all the monsters? To save all the people? It’s not going to happen! More and more of these creatures keep turning up and new demons are made. We keep going back to the same states even the same towns. Wouldn’t it have been better to have normal lives? To have a home, friends, a high school that we stay at for more than a year. ”

“This is who we are, this is what we are meant to do!” John yelled. “We are saving lives, we are helping people! I didn’t force you to join the hunt! I recall you begging to hunt with us, when I left you alone and Dean and I would hunt. You were miserable! You had no friends, no hobbies. You were desperate for some kind of excitement.”

“I was kid back then, I didn’t know what I was getting into!”

“Shut up! The two of you!” Dean shouted. “You guys are always at each other’s throats! For once I’d like us to just go on a hunt without you two arguing over the same shit!”

John parked the impala in front of Luke`s diner and they got out of the car. One by one they slammed the doors behind them.

Sam and Dean follow John into the diner. The family sit at the counter. Luke, a man in a red flannel shirt and a blue baseball cap came out of the kitchen. He had dirty blonde hair and brown eyes, he looked to be in his early 30s. Luke walked over to the Winchesters with a notepad in his hand.

”Are you guys ready to order?” Luke asked.

“Yeah we`ll get two burgers and a salad. “ John replied.

Luke wrote down their order on his notepad.

“Alright. Anything else?” he asked looking back at John.

“Yeah. What do you know about the deaths around here?” Dean asked.

Luke raised an eye brawl.

“The deaths? People get really old and then they die. Not much else to tell.”

“No, I’m talking about the 13 murders that happened.” Dean replied.

Luke laughed.

“Look, kid. I don’t know where you think you are? But nobody in this town has enough of a mean streak to kill anyone, let alone 13 people. The only people that die in this town are the elderly and even they take their sweet time with it.”

John went into his coat pocket and took out his fake FBI badge and shows it to Luke. The boys took out their badges as well.

“We are federal agents we know for a fact that there has been strange murders here.” John exclaimed. “We aren’t some reporters looking for a story or curious customers. We are here to do a job. Were here to fix what is going on here and all we want is some answers. Your shop is in the center of town. You must have heard or seen something.”

“There was no attack!” Luke yelled. “ Trust me I would know! I live in this town, and people love to gossip here! So if there was an attack, it wouldn’t be a secret! Also for your information there hasn’t even been any attack even remotely fitting your description anywhere in this state! If there was I’m sure it would be in the newspaper or on TV. Also I can tell those badges are fake. Look I don’t know if your insane or pulling some kind of prank but if you don’t want me to call the police, I would advise you to get out of my diner.”

Meanwhile as John continued speaking with Luke, Sam began to watch a beautiful girl as she entered the diner. She had straight long light brown hair and big blue eyes. Her skin was pale and her name was Rory. He watched as she walked past him and sat next to a women in her 30s with dark brown hair and the same blue eyes. The two women chatted and eventually some local boy, who had previously tried flirting with the mother, tried the same tactic with the daughter. Which ended in wise cracks and the local boy’s extreme embarrassment. Sam smiled he could tell by just watching her that Rory was a funny and down to earth girl, he liked that.

“Sam, Dean. Let’s go.” John spoke.

Just then a women walked in. She had her thin blonde hair in a ponytail and had dark brown eyes. She was dressed in a blue sweater, a white denim jacket and black jeans. Around her neck she had a white scarf. Holding hands with the women was a little girl with short blonde hair, dressed in a purple shirt with a pink coat and jeans. The little girl had a smile on her face and chubby cheeks, she looked no older than eight. The women smiled as she spotted John and the boys.

“John!” the women called out waving her free arm. The women and her daughter rushed over to the Winchesters. Her smile grew bigger as she came closer. She hugged John tightly. “I didn’t think you guys would actually come! This is so exciting!”

“Of course we`d come, you said-“ John began to say.

But Annie wasn’t listening, she was already hugging Sam and Dean. Both boys gave their father a look of discomfort and awkwardness.

“It’s so good to see you boys! the last time I saw the two of you was when you were babies, and now look at the two of you are men! We have a lot to of catching up to do!”

She hugged them again.

“Come sit and we`ll all chat.” She said with a smile as she made her way to an empty table.

“This girl is out of her mind.” Dean whispered to Sam.

Sam nodded.

“I think that’s a requirement to live here.” John commented to Dean.

But the three Winchester men followed Annie and sat down with her.

“Annie! Focus!” John shouted.

Annie turned her attention to her brother.

“You said that you were in danger.” John told her. “Annie, what’s going on? “

“Oh…well I kind of…just said that to get you here.” Annie admitted. “I knew you wouldn’t come if I had just asked. I thought my only chance of getting you here was to lie. I do need your help, though, it’s just not a monster thing.”

John rolled his eyes and looked at his sister with anger.

“Then what is it?” John asked, his voice stern.

Annie began to sob. 

“John, I know we haven’t been close in a really long time. But you used to be someone who I was always able to go to when things went wrong in my life. So, I’m asking for you to help me or tell me what to do…. I really need you now.”

Annie and John were ten years apart. The two shared the same mother, but different fathers. Their mother raised the two children together on her own. As kids John and Annie had always been close. John was always there to protect his odd little sister, who constantly was getting picked on. She didn’t like to stick to what was expected by society, she liked to move to her own beat. She was loud and outgoing and always was drawn to the strangest people. But she was kind, she had one of the biggest hearts. Annie sometimes had relied on John to be her friend, sometimes he`d be someone to protect her, then other times they`d be foes who would argue over foolish things. But as he looked at her crying, he knew he needed to be there for her. So John hugged her, then looked at his sister with compassion.

“Whatever is going on, I’m here for you. I’ll do whatever I can to help you, Annie.”

She smiled slightly and wiped the tears from her cheek.

“My husband left me a few months ago. Now it’s just me and Clare on our own. I had been able to work and get as much money as I can. It is not enough and I can’t take on any more hours because I must take care of Clare. The bills have started piling up now and I’m behind in rent. I just can’t do this on my own…maybe you guys can stay in town for a while and help me out, maybe watch her for a couple hours while I take on more hours or even a second job.”

“Or I can just give you some money. Wouldn’t that be easier?”

Dean and Sam watched as the scene unfolded. It was odd for them to see their father be nice or encouraging to anyone, he was never that kind of person toward them. Dean knew how it felt to have a sibling to look out for and the need to protect them at all cost. Dean understood why his father was doing all this.

“No! I know where you get your money and I don’t want to be a part of that.” She told him. “you have all those credit card schemes you pull, I’m not taking a chance with that.”

He sighed.

“Well I don’t want to see you work yourself to death. I know the kind of person you are, and you`ll regret It if you’re working so much that you don’t see your kid.” John spoke, he thought for a moment. “How about this....me and the boys will stay in town and work ordinary jobs and we`ll give you the money we earn.”

“how about half, so then you can have some for you and your boys.”

“You got yourself a deal.” He smiled and she smiled back.

“Thank you.” she spoke.

Annie lead the Winchesters back to her house. It was a big blue house on peach street with huge backyard. The home was two stories tall and as they walked in the home had a country style look to it.

“Home sweet home.” Annie spoke. “The guest room is down the hall, we only have one but we have a camp bed that I can move in there, obviously there is already a bed in there, and the couch pulls out into a bed so one of you can sleep there. Clare and I have rooms` upstairs.”

John nodded. Annie ran her figures through her hair, not knowing what to say next, a rare case for her. She looked at the boys and noticed Sam was the only one carrying a bag.

“So do you have more bags in the car? I can help you bring them in if you`d like.” Annie offered.

John smirked.

“We just have the one bag, we travel light.” John replied.

“Well I better get ready for work, I got to head out in a few hours. But if you`d like I’m sure Clare would be happy to show you guys around town. “

“That would be good we can start looking for jobs anyways.”

“I think Gypsy at the auto shop place is looking for full time workers, and there are a few places in town looking for part timers.”

“sounds good.”

Annie walked toward the stairs then turned back towards her brother.

“Thanks again, John. It really means a lot to me.” She spoke. Then headed up stairs.

John gave her a slight smile.

Clare lead John, Sam and Dean over to Gypsy`s shop. As they walked down the streets of the town people took notice of the outsiders.

“What’s wrong with these people? Why are they all staring at us?” Dean asked angrily. “It’s like they’ve never seen another person before.”

Clare chucked.

“Stars Hallow doesn’t get many get many tourist, thought Taylor would say otherwise, the only people who come into town are those who live here or the typical relatives of towns members.” Claire explained. “Everyone is really nice here, though, once you get to know them. I spent my whole life here, eventually everyone becomes like family. We all watch out for one another and befriend everyone.”

“That’s pretty cool.” Sam replied.

They waited for Gypsy to come out with applications, Kirk, a skinny 30 year old age with blonde hair walked over to the family.

“Do you know where Gypsy went? My mother wanted me to pick up her car for tomorrow.” Kirk spoke.

“She just went inside the garage to get applications for a job.” Sam spoke.

“Oh your looking for jobs! I can help you with that I have 32 jobs in town. There really easy to get around here and you really don’t need any experience. Although experience would be best, my mother once got a job at Miss Patty`s working as an assistant yoga instructor and as she tried to do this one move she got her legs stuck over her head for a week. I had to help bath her for a week.”

Sam, dean and Clare were trying very hard not to laugh.

“That’s awful, kirk. How did they fix her?” Clare asked.

“lots of medication and physical therapy.” Kirk replied. “The medication made her loopy though she was convinced that she was queen Elizabeth and began demanding things like crumpets and fine tea. She wouldn’t leave the house without a corset, do you know how hard it is to find a corset for 58 year old women.. very hard.”

Dean turned toward his father with a look of disgust and discomfort.

“How long are planning on making us stay here?” Dean whispered to his father.

“Just until we can get her back on her feet.” John replied. “…so probably a few month at the least.”

“A month?!” dean shouted with shock. “Are you serious!? Come on! We’re wasting our time here! Do you know how many cases were gana miss by staying here? Everyone looks at us around, like they know we don’t belong. I feel like if a cat got stuck in tree that would be the most interesting thing that ever happened here. Its creepy everyone is so happy and friendly. It’s not normal.”

Sam chuckled at the irony of that statement.

Gypsy made her way out of the auto shop and began to talk to John and Dean about a job. Since Sam was still in school, he needed a part time job. Clare suggested that Sam might be able to find a job at Doose`s market. They two made their way to the town square where all the shops and stores were located. As they walked in Sam saw Rory again. She was chatting with her friend, Lane. Lane was a Korean girl with big glasses and always seemed to be dressed like a punk rocker. Sam hid behind a nearby shelf, wanting to observe the type of girl Rory was.

“What are you doing?” Clare asked. Looking at Sam as if he were insane.

“Shh.” Sam whispered. “I don’t want her to see me.”

“Who? Lane?” Clare whispered back. “You don’t have a chance with her, her mom doesn’t let her date anyone that isn’t Korean.”

Sam sighed.

“No, the one that the Korean girl is talking to.”

Clare smiled as if she heard the juiciest secret.

“Oooh you like Rory!” she shouted, with a devious grin on her face.

“Clare. Shut up.” He whispered.

“Sam and Rory sitting in a tree K-I-S-S-I-N-G!” Clare sang aloud.

As Rory looked toward them, Sam quickly grabbed Clare and put his hand over her mouth. Clare continued to sing, Sam rolled his eyes.

“Didn’t you say we had to find some guy named Taylor about the job? How about you go look for him.”

“I`m not the one looking for the job.” Clare replied smugly.

“I’ll give you a dollar, if you go look for him and leave me alone.”

“Make it five.” She demanded.

“Deal.” He replied as he reached into his wallet and handed her the five. She took his money and walked over to another part of the store.

He watched Rory for a bit, trying to think of something clever to say to her. She was so smart and yet also odd, which he liked about her. He noticed Rory struggling to get a can off one of the top shelves. He took a deep breath and decided to swoop in to help her. He walked over and took the item she was reaching for then held it out to her. She smiled and took the can from his can.

“Thank you.” she spoke. “You know they really should put those on a lower shelf, they’re going to lose a lot of business this way.” she commented a bit awkwardly.

Sam chuckled.

“I agree, it’s not every day that someone freakishly tall will come to the rescue.”

She smiled then laughed.

“So, are you from around here?” Sam asked.

“Yeah I lived in Stars Hallow my whole life. My mom and I love this place, I couldn’t imagine living anywhere else.” She replied. “so, are you visiting someone here or are you moving in?”

“umm…. its undecided at this point.” He lied. “My family is visiting my aunt and were not sure how long were going to stay.”

“Well I can show you around, if you want- “

“Rory!” a raspy voice shouted. they turned to see a short heavy set middle aged women with blonde curly hair and brown eyes coming their way.

“Rory!” the women called out again. “Your never gana believe what happened. I let your mother watch my cat for 15 minutes while I went to get groceries. My husband just got home and he said the cat is acting all crazy now! I don’t understand it; your mother is like poison to animals. Now I got to get the cat its medicine while I’m out.”

“Oh, I’m sorry to hear that, Babette.” Rory replied. Suddenly Rory`s phone began to ring.

“It’s my mom, she is probably wondering where I am. I should head home.” She spoke. She turned to Sam. “It was nice talking with you.”

Babette looked Sam up and down.

“you must be one of Annie`s nephews.” Babette commented. “She was talking about trying to get her brother and his kids to come into town. Didn’t think it would actually happen, she has been talking about getting you guys here for years.”

“Really?” he questioned.

Babette nodded.

“Oh yeah. She always talks about how much she missed her family, her and her brother used to be real close. She has a lot of wacky stories that she tells about the two of them, her and her brother got into all sorts of trouble as kids. Anyways tell me about you? what’s your name? Annie said she had two nephews, where is the other one? How long are you staying?”

He looked at Babette with a look of confusion. _What was with all the questions? _He thought. _Where should he even start?_

“My name is Sam, my brother`s name is Dean. My dad and my brother are looking for jobs at the auto shop. I’m not I`m not sure how long were staying.”

Babette`s phone rang.

“Hold on, Dean.” She said to Sam, clearly having had mixed up the names.

“oh, I’m not- “

“I’m coming home right now! I promise!” Babette said into the phone. She looked over same “I`m sorry, got to go, Dean. My cats need me right away! I`ll see you soon.”

As Babette left Sam could hear snickering from behind him. He turned and saw Clare standing there.

“Well looks like your Dean now, unless you want to go around correcting the whole town.” Clare told him. “Babette is the town gossip, she talks to every single person she sees. Each person she will tell the latest news to, which today will be your family`s arrival. When she talks about how she met you, and most likely describes you, she`ll be calling you dean. This is a small town her gossip travels fast, it’s probably already too late to fix it.”

“Come on news can’t travel that fast.” Sam corrected.

Suddenly Miss Patty and Kirk enter the market and pass by Sam.

“Hi Dean.” Kirk spoke while passing by Sam.

“Hi Dean.” Miss patty called out, as she passed him too.

Clare chuckled.

“I told you.” Clare said to Sam.


End file.
